diff --git a/backend/internal/api/knowledgeHub.go b/backend/internal/api/knowledgeHub.go
index 8cb21f4..3a7057a 100644
--- a/backend/internal/api/knowledgeHub.go
+++ b/backend/internal/api/knowledgeHub.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"net/http"
+	"strings"
 	"time"
 
 	"github.com/danielgtaylor/huma/v2"
@@ -65,6 +66,13 @@ func (a *api) registerKnowledgeHubRoutes(_ chi.Router, api huma.API) {
 		Path:        prefix + "/{uuid}/related",
 		Tags:        tags,
 	}, a.createRelatedArticleHandler)
+
+	huma.Register(api, huma.Operation{
+		OperationID: "generateTableOfContents",
+		Method:      http.MethodPost,
+		Path:        prefix + "/{uuid}/generate-toc",
+		Tags:        tags,
+	}, a.generateTOCHandler)
 }
 
 type GetKnowledgeArticlesOutput struct {
@@ -118,6 +126,16 @@ type CreateRelatedArticleInput struct {
 	} `json:"body"`
 }
 
+type GenerateTOCInput struct {
+	UUID string `path:"uuid"`
+}
+
+type GenerateTOCOutput struct {
+	Body struct {
+		TableOfContents []domain.TableOfContent `json:"table_of_contents"`
+	} `json:"body"`
+}
+
 func (a *api) getAllKnowledgeArticlesHandler(ctx context.Context, input *struct{}) (*GetKnowledgeArticlesOutput, error) {
 	resp := &GetKnowledgeArticlesOutput{}
 
@@ -285,3 +303,70 @@ func (a *api) createRelatedArticleHandler(
 
 	return nil, nil
 }
+
+func generateTOCFromContent(content string) []domain.TableOfContent {
+	var toc []domain.TableOfContent
+	lines := strings.Split(content, "\n")
+	order := 0
+
+	for _, line := range lines {
+		line = strings.TrimSpace(line)
+		if strings.HasPrefix(line, "# ") {
+			order++
+			toc = append(toc, domain.TableOfContent{
+				Title: strings.TrimPrefix(line, "# "),
+				Level: 1,
+				Order: order,
+			})
+		} else if strings.HasPrefix(line, "## ") {
+			order++
+			toc = append(toc, domain.TableOfContent{
+				Title: strings.TrimPrefix(line, "## "),
+				Level: 2,
+				Order: order,
+			})
+		} else if strings.HasPrefix(line, "### ") {
+			order++
+			toc = append(toc, domain.TableOfContent{
+				Title: strings.TrimPrefix(line, "### "),
+				Level: 3,
+				Order: order,
+			})
+		}
+		// Add more levels if needed
+	}
+
+	return toc
+}
+
+func (a *api) generateTOCHandler(
+	ctx context.Context,
+	input *GenerateTOCInput,
+) (*GenerateTOCOutput, error) {
+	resp := &GenerateTOCOutput{}
+
+	// Validate UUID format
+	if _, err := uuid.FromString(input.UUID); err != nil {
+		return nil, huma.Error400BadRequest("invalid UUID format")
+	}
+
+	// Get the article
+	article, err := a.knowledgeHubRepo.GetArticleByID(ctx, input.UUID)
+	if err != nil {
+		if errors.Is(err, domain.ErrNotFound) {
+			return nil, huma.Error404NotFound("article not found")
+		}
+		return nil, err
+	}
+
+	// Generate TOC from content
+	tocItems := generateTOCFromContent(article.Content)
+
+	// Save to database
+	if err := a.knowledgeHubRepo.CreateTableOfContents(ctx, input.UUID, tocItems); err != nil {
+		return nil, huma.Error500InternalServerError("failed to save table of contents")
+	}
+
+	resp.Body.TableOfContents = tocItems
+	return resp, nil
+}
diff --git a/backend/internal/domain/knowledgeHub.go b/backend/internal/domain/knowledgeHub.go
index 04ad316..9cdf08b 100644
--- a/backend/internal/domain/knowledgeHub.go
+++ b/backend/internal/domain/knowledgeHub.go
@@ -42,12 +42,13 @@ func (k *KnowledgeArticle) Validate() error {
 }
 
 type TableOfContent struct {
-	UUID      string
-	ArticleID string
-	Title     string
-	Order     int
-	CreatedAt time.Time
-	UpdatedAt time.Time
+	UUID      string    `json:"uuid"`
+	ArticleID string    `json:"article_id"`
+	Title     string    `json:"title"`
+	Level     int       `json:"level"`
+	Order     int       `json:"order"`
+	CreatedAt time.Time `json:"created_at"`
+	UpdatedAt time.Time `json:"updated_at"`
 }
 
 type RelatedArticle struct {
@@ -60,13 +61,18 @@ type RelatedArticle struct {
 }
 
 type KnowledgeHubRepository interface {
+	// Article methods
 	GetArticleByID(context.Context, string) (KnowledgeArticle, error)
 	GetArticlesByCategory(ctx context.Context, category string) ([]KnowledgeArticle, error)
 	GetAllArticles(ctx context.Context) ([]KnowledgeArticle, error)
 	CreateOrUpdateArticle(context.Context, *KnowledgeArticle) error
 	DeleteArticle(context.Context, string) error
 
+	// Table of Contents methods
 	GetTableOfContents(ctx context.Context, articleID string) ([]TableOfContent, error)
+	CreateTableOfContents(ctx context.Context, articleID string, items []TableOfContent) error
+
+	// Related Articles methods
 	GetRelatedArticles(ctx context.Context, articleID string) ([]RelatedArticle, error)
 	CreateRelatedArticle(ctx context.Context, articleID string, related *RelatedArticle) error
 }
diff --git a/backend/internal/repository/connection.go b/backend/internal/repository/connection.go
index 63d6305..0d0c99e 100644
--- a/backend/internal/repository/connection.go
+++ b/backend/internal/repository/connection.go
@@ -11,4 +11,5 @@ type Connection interface {
 	Exec(context.Context, string, ...interface{}) (pgconn.CommandTag, error)
 	Query(context.Context, string, ...interface{}) (pgx.Rows, error)
 	QueryRow(context.Context, string, ...interface{}) pgx.Row
+	BeginTx(ctx context.Context, txOptions pgx.TxOptions) (pgx.Tx, error)
 }
diff --git a/backend/internal/repository/postgres_knowledgeHub.go b/backend/internal/repository/postgres_knowledgeHub.go
index 75925a1..53b983d 100644
--- a/backend/internal/repository/postgres_knowledgeHub.go
+++ b/backend/internal/repository/postgres_knowledgeHub.go
@@ -2,6 +2,8 @@ package repository
 
 import (
 	"context"
+	"fmt"
+	"github.com/jackc/pgx/v5"
 	"strings"
 
 	"github.com/forfarm/backend/internal/domain"
@@ -213,3 +215,51 @@ func (p *postgresKnowledgeHubRepository) CreateRelatedArticle(
 	)
 	return err
 }
+
+func (p *postgresKnowledgeHubRepository) CreateTableOfContents(
+	ctx context.Context,
+	articleID string,
+	items []domain.TableOfContent,
+) error {
+	// Begin transaction
+	tx, err := p.conn.BeginTx(ctx, pgx.TxOptions{})
+	if err != nil {
+		return fmt.Errorf("failed to begin transaction: %w", err)
+	}
+	defer func() {
+		if err != nil {
+			tx.Rollback(ctx)
+		}
+	}()
+
+	// First delete existing TOC items for this article
+	_, err = tx.Exec(ctx, `DELETE FROM table_of_contents WHERE article_id = $1`, articleID)
+	if err != nil {
+		return fmt.Errorf("failed to delete existing TOC items: %w", err)
+	}
+
+	// Insert new TOC items
+	for _, item := range items {
+		item.UUID = uuid.New().String()
+		_, err = tx.Exec(ctx, `
+            INSERT INTO table_of_contents 
+            (uuid, article_id, title, level, "order", created_at, updated_at)
+            VALUES ($1, $2, $3, $4, $5, NOW(), NOW())`,
+			item.UUID,
+			articleID,
+			item.Title,
+			item.Level,
+			item.Order,
+		)
+		if err != nil {
+			return fmt.Errorf("failed to insert TOC item: %w", err)
+		}
+	}
+
+	// Commit transaction
+	if err := tx.Commit(ctx); err != nil {
+		return fmt.Errorf("failed to commit transaction: %w", err)
+	}
+
+	return nil
+}
diff --git a/backend/internal/service/toc_generator.go b/backend/internal/service/toc_generator.go
new file mode 100644
index 0000000..7f85f6a
--- /dev/null
+++ b/backend/internal/service/toc_generator.go
@@ -0,0 +1,37 @@
+package service
+
+import (
+	"github.com/forfarm/backend/internal/domain"
+	"regexp"
+	"strings"
+)
+
+type TOCGenerator struct{}
+
+func NewTOCGenerator() *TOCGenerator {
+	return &TOCGenerator{}
+}
+
+func (g *TOCGenerator) GenerateFromContent(content string) []domain.TableOfContent {
+	var toc []domain.TableOfContent
+	lines := strings.Split(content, "\n")
+	order := 0
+
+	headerRegex := regexp.MustCompile(`^(#{1,6})\s+(.*)$`)
+
+	for _, line := range lines {
+		if matches := headerRegex.FindStringSubmatch(line); matches != nil {
+			order++
+			level := len(matches[1]) // Number of # indicates level
+			title := matches[2]
+
+			toc = append(toc, domain.TableOfContent{
+				Title: title,
+				Level: level,
+				Order: order,
+			})
+		}
+	}
+
+	return toc
+}
diff --git a/backend/migrations/00004_create_knowledge_hub_tables.sql b/backend/migrations/00004_create_knowledge_hub_tables.sql
index 4d8b722..01598de 100644
--- a/backend/migrations/00004_create_knowledge_hub_tables.sql
+++ b/backend/migrations/00004_create_knowledge_hub_tables.sql
@@ -13,13 +13,13 @@ CREATE TABLE knowledge_articles (
 );
 
 CREATE TABLE table_of_contents (
-                                   uuid UUID PRIMARY KEY DEFAULT gen_random_uuid(),
-                                   article_id UUID NOT NULL,
-                                   title TEXT NOT NULL,
-                                   "order" INT NOT NULL,
-                                   created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
-                                   updated_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
-                                   CONSTRAINT fk_toc_article FOREIGN KEY (article_id) REFERENCES knowledge_articles(uuid) ON DELETE CASCADE
+    uuid UUID PRIMARY KEY,
+    article_id UUID NOT NULL REFERENCES knowledge_articles(uuid),
+    title TEXT NOT NULL,
+    level INT NOT NULL,
+    "order" INT NOT NULL,
+    created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    updated_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
 );
 
 CREATE TABLE related_articles (